The Chick Flick Moments of Bobby and Crowley
by akiddep
Summary: How did Crowley get into that trailer?  07 X 01  Bobby gave it to him; because a long time ago Crowley helped Bobby out of his wheelchair. Crowley is not the Devil you know and Bobby would agree.


Title: The Chick flick moments of Bobby and Crowley

Pairing: Bobby/ Crowley, with implied Crowley/Cas, Crowley/Sam, Crowley/Dean, and Crowley/Raphael

Category Romance

Rated M for graphic sex

Disclaimer: I don't own Supernatural or any of its characters but I wish I did.

Summary: How did Crowley get into that trailer? (07 X 01) Bobby gave it to him; because a long time ago Crowley helped Bobby out of his wheelchair. Crowley is not the Devil you know and Bobby would agree.

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Nothing in this world comes for free. Bobby should have known that! He could kick himself in the head for standing up out of that wheelchair. "Demons don't do anything for free, especially Crowley," he thought to himself.

It was too late now. He was walking around on two good legs and Crowley was on his doorstep looking for payment. It was bad enough the demon had his soul; now he wanted Bobby to bend over like a prison bitch in the shower looking for soap.

So Bobby Singer dropped his pants and bent over his desk waiting for Crowley to get things started.

"I ain't taking my hat off!" the old drunk grumbled to the demon, the Crossroads King.

"Whatever makes you comfortable, darling."

"Comfortable? Yeah, I can tell you what…. Awww" The hunter was surprised to feel the demon's finger on his entrance. Crowley was slowly circling his finger around the hunter's whole. Crowley is never concerned in making the other happy, he just likes to hear them moan; but this time he truly wanted to show "The Bobby Singer" what the King of Hell was really capable of.

He slowly inserted his middle finger inside the hunter and was surprised when Bobby didn't cry out. Not too many people can take it dry. Of course, it was the old grump's way of not showing weakness. So if Crowley couldn't make him scream out in pain he was just going to have to make in moan in pleasure. Not an experience he gets to have all the time.

Crowley conjured up a bottle of lube and smeared it down Bobby's backside. It was cold and the hunter shivered to the touch. This time Crowley entered two fingers into the hunter and he watched how Bobby hunched over with pain but never said a word. Damn, that hunter, he thought. He curled his fingers and watched Bobby Singer lose control.

Crowley pumped his fingers in and out as fast as humanly possible and listened to the sounds that escaped the hunter's mouth.

"Crowley, please."

Now that was unexpected! The Bobby Singer begging him to continue, begging to be fucked by him – Crowley, The Crossroads King of Hell. He thought he'd get a sweet little whimper but this almost sounded affectionate. "Oh well might as well continue," he thought to himself.

He slicked his cock up with lube and shoved his whole price inside. God, was the man tight. Still Bobby Singer didn't make a sound; it was like his begging Crowley to continue never happened. Crowley went right on ahead anyway – thrusting in and out – working himself up good. And then he heard it.

Bobby Singer cried out when Crowley hit his sweet spot.

"I knew I'd make you scream." Crowley made sure that every thrust was dead on to the old man's prostate. Soon afterwards Bobby was pushing back to met Crowley thrust for thrust. Bobby was moaning louder and louder, he was getting close to his finish.

Bobby knew he should have been angry that a demon brought him this close to the edge, but he wasn't, he hadn't felt this good in years. He knew he should have been shamed for moaning like a bitch in heat every time Crowley pushed his manhood in him but by this point all Bobby Singer wanted to do was cum. He reached his hand in front of him and pulled on his dick as hard as he could.

Crowley wasn't exactly sure why but he felt obligated to touch the man so he rubbed his hands up and down the man's back and chest. He pushed his nose into the man's neck and smelled sweat, beer, and gasoline. It smelled the way a man like Bobby Singer should smell. Crowley loved it.

"Crowley." Bobby leaned his head back into the demon's shoulder as he came all over his hand and desk. Bobby wasn't sure why but when Crowley kissed him he opened his mouth and let him invade it. It wasn't like the Crossroads kiss, so stiff and confined, it was sweet and enduring.

Bobby Singer woke up the next morning on his couch alone. Crowley and his soul were no where in sight.

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Crowley sat a bar drinking whatever the bar maid tossed at him. Damn that old drunk fool! Crowley couldn't concentrate on what to do next. Bobby Singer forced him to give him back his soul for his bones; but Bobby Singer should have just light him up in flames. Any other hunter would have done it. And any other hunter won't have given him his bones to hide forever.

Was this Bobby Singer's way of trying to show he was interested? Crowley kept replaying that kiss over and over in his mind. The way Bobby leaned back into him and kissed him with his mouth open.

Oh, he was going to need a lot more alcohol before he can figure this out.

A few hours later a very drunk Crowley once again showed up at Bobby Singer's place because he was sure that he figured it out.

"Hello, darling."

"Well it took you long enough, idgit." Bobby said sitting behind his office desk

"It wasn't like you put up in a candle in the window." Crowley said approaching the hunter. "You are a hard man to figure out."

"Are you drunk?"

"Yeah I am. And take off that fucking hat." Crowley grabbed Bobby's hat and threw it across the room. Bobby got up off his chair and grabbed Crowley's suit. No one messes with his hat.

Before Bobby could even hit him Crowley kissed him; this time it started slowly. They began working to take off each other's clothes. Their hands roamed each other's bodies, well; Crowley's hands were roaming around Bobby's body. The demon was so drunk Bobby was sure he won't be doing half this stuff if he was sober; like, dropping to his knees and taking Bobby in his mouth.

It felt good but the man was awkward. Crowley wasn't exactly sure what he doing. Mostly Crowley just bobbed his head; but hell Bobby hadn't had anyone's mouth around him in a while so it wasn't like he was complaining. If the demon was going to suck him off he wasn't going to push him away.

It got weird when Crowley laid Bobby down on his desk and then spread his legs. Crowley didn't really wait around to hear Bobby's complains he just stuck his tongue out and licked Bobby's entrance. Yeah, Crowley would have to be drunk to do this; Bobby doubted he would be doing this sober.

Crowley pushed his tongue passed the first layer of muscle and pushed until his nose met Bobby's skin. He rubbed his teeth down on the man's entrance and felt him squirm. He continued to get Bobby wet and gave him one last lick from his entrance to the tip of his cock. He spit on his hand and slicked himself up.

Bobby moaned as Crowley pushed himself into him. Damn, it hurt even after the last time Crowley fucked him. But he didn't care Crowley felt good inside of him and on top of him. Bobby clawed his way down Crowley's back as the demon thrust this way and that to find that sweet spot.

Crowley found it and Bobby sang like he was Johnny Cash! Even drunk that demon pushed him to the edge. This time it was Crowley's hand pumping his dick when he came. Crowley came inside of him soon after.

It took both men a long while to catch their breath.

"Crowley, we are too old to be sleeping in this position." With the snap of his fingers Crowley had them both in Bobby's bed. This time Crowley stayed until morning.

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Bobby knew that Crowley was still a demon no matter how close they became, but he didn't know that this demon was a masochist. Some crossroad deals took a lot more than just a kiss with the king of Hell and some kinds of clients required Crowley to be a little more ruff than usual. Bobby knew that and he was fine with it; Crowley always came back to him, but Crowley wasn't okay with this.

Bobby knew about Crowley's deal with Castiel, the Angel of Thursday. Bobby knew for that deal Crowley bent the angel over and fucked him. He knew about Crowley recruiting Samuel and soulless Sam to hunt alphas; and Sam ended up on his knees on several occasions to service Crowley. When Dean thought Crowley owed his baby brother's soul, Crowley used that to make the boy spread his legs. It was the only way Crowley could keep his employees in line. Then came Raphael after Castiel broke their deal, that Archangel wasn't too happy with Crowley's deal making, which is why he got a women vessel.

But at the end of the day Crowley was always in Bobby's bed. Bobby always knew when Crowley had been with someone else before stopping by. It was the oddest thing about his demon; Crowley could never penetrate him when he had already penetrated someone else. He always wanted Bobby to fuck the shit out of him though. The more it hurt the better for him because Crowley hated when Bobby never punished him for his indiscretions.

Bobby was happy to indulge in Crowley's fantasies.

He would bend Crowley over his knee and spank him until the demon came all over himself. Sometimes Crowley wanted him to use a belt or some piece of leather lying around the house. Bobby loved to hear it *smack* against the demon's ass. Crowley would cry out in pain and arousal until he reached his climax. Then Bobby would get to fuck his tight pink ass until the demon was crying out again underneath him.

Crowley loved to be dominated almost as much as Bobby liked to dominate. Maybe that's why he still kept running around and making deals because you knew Bobby loved to punish him. Bobby loved to push him down on his knees and fuck his mouth, loved to brush his skin so everyone would know Crowley was taken.

But Crowley knew when it was over Bobby would clean him up and put him in their bed. They would sleep holding each other all through the night. Crowley knew was still a demon, and would probably never be human, but that was okay as long as Bobby Singer stayed his hunter.

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As soon as the Angel of Thursday become God!stiel, Crowley took off. He left Bobby because he knew the new God was either going to kill him or had some another kind of plan for him. He wasn't going to stick around and find out. He hoped that Bobby knew that; that he left because he knew God!stiel would spare Bobby's life. If he though God!stiel was going to kill him be would have stayed.

Bobby did know. When Crowley finally made it back to his place when it was all over he was glad and welcomed the demon back with open arms. He was glad that the demon was able to get away; but the fight wasn't over yet. God!stiel was still out there smiting people.

"You fucking idgit, you need to stay hidden."

"Well, hello to you too, darling." Crowley didn't waste much time, he attached the hunter's lips. He pulled away to snap them into the bedroom with Bobby underneath him. "If I'm gonna go into hiding at least let me fuck you one more night."

Bobby couldn't say no to that. The demon snapped their clothes away, except the hat (Bobby's orders), and conjured up a big bottle of lube. He coated his fingers and pushed one inside Bobby with no warning. The man was tight since he hadn't bottom in a while. He circled it around and pulled it slightly out to insert another one.

"You want to slow it down there. I'm not as young as I use to be," the hunter said.

"Don't worry darling; tonight you will be. I happen to know a crossroads demon that can make it happen."

"Oh, is that right…" Crowley kissed the man before he could finish; his hunter like to talk a lot and Crowley wasn't in a talking mood.

While the hunter was distracted he inserted a third finger and the man wiggled underneath him in pain and pleasure. Crowley quickly pulled his fingers in and out to find that sweet spot. He was rewarded with a loud moan. He stimulated the man's prostate until he was shooting pre-cum and then as quickly as they were added Crowley pulled his fingers away.

Bobby moaned at the loss of stimulation but the demon was quick to slick himself up and enter the man.

"You really are a beautiful sight for a human."

"You ain't so bad yourself, demon."

Crowley smiled to himself; Bobby Singer always was the charmer. He took his rhythm slow, since Heaven knew when he would be able to do this again; he wanted to make this last all night. It didn't exactly go as planned. The hunter clawed down his back until he speed up to a pace they both enjoyed. Before Crowley even knew it, they were both crying out in release. He loved the white warmth that coated his stomach.

They were silent most of the night. Neither one wanted to sleep if this was going to be a last night of sex for a while; but finally the hunter spoke, "If he finds you, he will kill you."

"Don't worry about that love. He just wants me to stand around looking pretty, and I am very good at doing just that."

"That's about all you are good for," the hunter replied back.

"That's not nice love," Crowley spat back. "I got some more tricks up my sleeve."

"Uh, um. Don't worry about it. I already have a plan."

XXXXXXX

Bobby was so pleased when the summoning spell for Crowley worked; but the demon looked like hell. He was definitely trying to drink himself into oblivion. Not that the hunter could blame him; if it wasn't for the boys then he would be doing the same thing. He hoped that this new threat would be over soon because he had a date with his demon when this was all said and done.


End file.
